Pd-Catalyzed Regioselective Direct Double C-H Arylation of 6,7-Benzindoles

被引：7
|
作者：
Li, Ping-Gui [1 ,2 ]
Yang, Youqing [1 ]
Zhu, Shuai [2 ]
Li, Hong-Xi [2 ]
Zou, Liang-Hua [2 ]
机构：
[1] Nanjing Univ, State Key Lab Coordinat Chem & Chem Engn, Xianlin Ave 163, Nanjing 210093, Jiangsu, Peoples R China
[2] Jiangnan Univ, Sch Pharmaceut Sci, Lihu Ave 1800, Wuxi 214122, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 01期
关键词：
6,7-Benzindole; Diarylation; C-C coupling; C-H activation; Palladium; N-PIVALOYLINDOLES; INDOLES; FUNCTIONALIZATION; MILD; FORMYLATION; OLEFINATION; ACTIVATION; ALKYLATION; CYANATION; ACCESS;
D O I：
10.1002/ejoc.201801473
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A palladium-catalyzed protocol for the first direct diarylation of 6,7-benzindoles with aryl iodides at the C4 and C5 positions was developed. The key to this strategy was the employment of pivaloyl as the directing group at the C3 position and the blocking effect at the C6 and C7 positions. The reaction proceeded very well, providing a series of diarylated 6,7-benzindoles without prefunctionalization at the reactive sites. Several examples on the unexpected monoarylation of 6,7-benzindoles at the C5 position were also presented.
引用
收藏
页码：73 / 76
页数：4
相关论文
共 50 条
  • [31] Palladium-Catalyzed Direct Arylation of Azulene Based on Regioselective C-H Bond Activation
    Murai, Masahito
    Yanagawa, Mayu
    Nakamura, Masahiro
    Takai, Kazuhiko
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (05) : 629 - 635
  • [32] Iridium(III)-catalyzed regioselective direct arylation of sp2 C-H bonds with diaryliodonium salts
    Gao, Pan
    Liu, Li
    Shi, Zhuangzhi
    Yuan, Yu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (29) : 7109 - 7113
  • [33] Direct synthesis of 3-arylquinolines by a nano Pd-catalyzed regioselective C3-H arylation of quinolines
    Paul, Abhijit
    Paul, Aditya
    Yadav, Somnath
    TETRAHEDRON LETTERS, 2020, 61 (01)
  • [34] Pd(II)-catalyzed β-C-H arylation of O-methyl ketoximes with iodoarenes
    Mu, Yucheng
    Tan, Xiaodong
    Zhang, Yemin
    Jing, Xiaobi
    Shi, Zhuangzhi
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (03): : 380 - 384
  • [35] Pd(II)-catalyzed direct C5-arylation of azole-4-carboxylates through double C-H bond cleavage
    Li, Ziyuan
    Ma, Ling
    Xu, Jinyi
    Kong, Lingyi
    Wu, Xiaoming
    Yao, Hequan
    CHEMICAL COMMUNICATIONS, 2012, 48 (31) : 3763 - 3765
  • [36] Ligand-Free Pd-Catalyzed Direct C-H Arylation of Polyfluoroarenes with Aryl Iodides under Ambient Air Conditions
    Budiman, Yudha P.
    Tasripin, Pambudi A.
    Ramadhan, Muhammad R.
    Hannifah, Raiza
    Deawati, Yusi
    Mayanti, Tri
    Solihudin, Miftahussurur H.
    Putra, Miftahussurur H.
    Radius, Udo
    Marder, Todd B.
    CHEMISTRY-AN ASIAN JOURNAL, 2025,
  • [37] Dioxazolones as masked ester surrogates in the Pd(ii)-catalyzed direct C-H arylation of 6,5-fused heterocycles
    Saxena, Paridhi
    Maida, Neha
    Kapur, Manmohan
    CHEMICAL COMMUNICATIONS, 2019, 55 (75) : 11187 - 11190
  • [38] Direct arylation of cyclic enamides via Pd(II)-catalyzed C-H activation
    Zhou, Hai
    Chung, Wan-Jun
    Xu, Yun-He
    Loh, Teck-Peng
    CHEMICAL COMMUNICATIONS, 2009, (23) : 3472 - 3474
  • [39] Pd-Catalyzed Asymmetric Allylic C-H Functionalization
    Wang, Pu-Sheng
    Gong, Liu-Zhu
    CHINESE JOURNAL OF CHEMISTRY, 2023, 41 (15): : 1841 - 1848
  • [40] The Dual Effect of the Acetate Ligand on the Mechanism of the Pd-Catalyzed C-H/C-H Coupling of Benzene
    Beckers, Igor
    Henrion, Mickael
    De Vos, Dirk E.
    CHEMCATCHEM, 2020, 12 (01) : 90 - 94
12345